Direct N-cyclopropylation of cyclic amides and azoles employing a cyclopropylbismuth reagent

Journal of the American Chemical Society

Volumn 129, Issue 1, 2007, Pages 44-45

  Gagnon, Alexandre ^a   St Onge, Miguel ^a   Little, Kelly ^a   Duplessis, Martin ^a   Barabé, Francis ^a  

^a BOEHRINGER INGELHEIM CANADA LTD   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; BISMUTH DERIVATIVE; CYCLOPROPANE DERIVATIVE; PYRROLE DERIVATIVE; REAGENT;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL MODIFICATION; CHEMICAL REACTION; CHEMICAL STRUCTURE;

AMIDES; AZOLES; CYCLOPROPANES; ORGANOMETALLIC COMPOUNDS;

EID: 33846093068     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0676758     Document Type: Article

References (32)

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25. 1H NMR showed the presence of one set of signals for the cyclopropyl group, supporting a structure with equivalent cyclopropanes.
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27. 1H NMR was identical after contact with air and trituration. Gravimetric and elemental analyses showed that the solid contains 61.5% bismuth, 19.28% carbon, and 2.33% hydrogen. Minor loss of reactivity is observed after 2 weeks when the reagent is stored in the freezer under argon.
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30. The N-cyclopropylation reaction of amide 3 failed when reagent 2a was generated in situ. In a separate experiment, the presence of a large amount of magnesium salts was found to completely shut down the cyelopropyl transfer.
31. Starting material was completely consumed.
32. Imidazoles, acyclic amides, and amines did not undergo N-cyclopropylation under the conditions reported in this paper.